Holmes Wilson is Driven By | I don’t completely know, but it’s something like: I have a feeling that I have something unique to contribute to the world, so I’m trying to do that, while along the way getting a better idea of what I have to contribute.
My Highlights | I’ve done two things in my life that I feel were truly, deeply great. One was right after starting Fight for the Future, where we were able to organize a series of protests and actions that lead to the pretty-much spontaneous Internet uprising that stopped “SOPA”, the American Internet censorship bill.
The other thing, and it’s funny to say this, was a large party I organized in the summer of 2000. It’s a long story which doesn’t fit here, but for me I’d say it was about 1/10th as good as defeating SOPA. There have been lots of other achievements and adventures along the way, but nothing that feels big in comparison to these two.
A Key Talent | I’m going to challenge the question a bit and approach it from another angle, because I don’t think so much of this is about innate talents or deliberately acquired habits.
It was really helpful for me to have an intense and wide open educational experience when I was 15-17 years old. If you’re a parent, try to give your kid that. I also benefited immensely from being able to start my work in my early twenties living at home with my parents, with pressure to use my talents but without pressure to make money. If you’re a parent, I think you should try to give your kids that too.
If you don’t have that kind of support from parents, there are things you can do (by being entrepreneurial or creatively frugal) to try to create a material cushion for yourself, though I recognize it’s a lot harder. But, if you’re serious about changing the world you need to create some position that leaves you with free time and the ability to take risks, as soon as you can in life.
The Characteristics Of Success | I think getting quickly unsatisfied has helped me a lot actually. If you’re bored, or feel like you’re spinning your wheels, or everything seems meaningless, don’t work too hard to repress that feeling; listen to it. If it’s real, make a plan to change it.
Sometimes you get false alarms though, so you also have to learn to see through those and stay the course. I think I’m getting better at that.
Lessons I Have Learnt | One important lesson is that almost nobody knows what the hell they’re talking about, really, when it comes to talking about complex human systems (things like politics, society, the economy, culture, etc.) People make bogus predictions and state them as fact, all the time.
Usually when people sound very smart and sure of themselves, it means they’ve dedicated their talents to that, that is, to sounding really smart and sure of themselves. The people who are best at doing things often have a terribly hard time articulating how they do it.
It’s like asking a pro tennis player about tennis; they’re obviously great at tennis, but they won’t really be able to tell you anything that you can use for playing tennis. They’re also more likely to win a match than the world’s greatest tennis lecturer or theorist.
Dealing With Doubt | The trick for me has been to work with other great people, and to avoid changing course too quickly based on these feelings.
Performing At My Peak | Maybe some people can do that, but I can’t. There are inevitable peaks and troughs of energy, for me, and for most people I know. I think humans were built that way.
For me, the trick is trying to make sure that I’m performing at my peak in the less frequent moments when I really need to be. That means listening to your instincts and getting some rest in moments that seem like downtime, but being ready to gear up immediately when there’s an opportunity or need.
Resources I Use To Stay Inspired | I think everybody young should read classics and avoid new stuff, especially when it comes to fiction. Time is the best filter for what’s good.
Advice On Building Wealth | Quickly build a cushion you can fall back on (or figure out how to use the one you have well) and then start doing risky things with limited cost (measured not just in money, but also hours of your day or months of your life) and unlimited upside.
Do as many things as you can manage in a coherent way (some things you’ll need to focus on completely for years, but some stuff is a decision you can make an instant, like the decision to invest money in a friends’ start-up, say). Most of your success will come in a few unusual moments.
Also, if you feel drawn to doing something that has absolutely no material return, please do it. You’ll be able to figure out the money side of things later, or in parallel, through side entrepreneurship or frugality.
The thing the world needs more desperately than anything are people who are able to work 100% on something with absolutely no material return. Everyone else, no matter how successful they are, is just a cog in a machine–one that we know isn’t necessarily doing good things for or with humanity. People who work passionately for a result that has nothing to do with a pay check are the only ones standing outside that machine, so they’re the only ones who can truly guide it in a better direction, to make sure it doesn’t destroy itself/us.
On Inspiring Others | The way that’s worked the best for us is to put our own best energy and work out into the world. That ends up connecting you with other good people and to the extent you inspire them they’ll want to work with you.
That’s true whether it’s people you hire, people who will hire you, or allies out there in the world.
I Am Inspired By | The people who inspire me the most are people who end up in the right place and the right time with the right abilities, and make an extraordinary effort to fit their abilities to what they think the world needs in that moment. That’s what I aspire to most deeply.
I really do believe that most of the best ones are very invisible to history, and that’s why the names that come to mind are very odd:
The anonymous creator of Bitcoin.
(Re: Stallman, I know he’s a very odd duck, interpersonally. But the vision he had in the 80’s and the activism he did both around free software and in promoting an ethics of technology worked so well. This is a stretch but I’m not sure if we’d have Snowden, or Bitcoin, without him).
It’s funny to say this but I don’t think I have any role models, except in the sense that I have close friends or colleagues whose qualities I admire. Sometimes along the way you see people who are doing what you want to be doing, but that’s more rare and fleeting and happened more when I was younger. That could be because I’m on such a strange path.